Ethanol → [1-Methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethyl(4-chlorobenzyl)ammonium iodide

HRID 1288518Notes

Reaction equation

HRID 1288518 reaction equation
[CH3:1][CH:2]([N:14]([CH3:16])[CH3:15])/[CH:3]=[CH:4]/[CH:5]1[C:10]([CH3:12])([CH3:11])[CH2:9][CH2:8][CH:7]=[C:6]1[CH3:13].Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1.C(O)C.[I-:29].[K+]>O>[I-:29].[CH3:1][CH:2]([N+:14]([CH3:16])([CH3:15])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)/[CH:3]=[CH:4]/[CH:5]1[C:10]([CH3:11])([CH3:12])[CH2:9][CH2:8][CH:7]=[C:6]1[CH3:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 4875Potassium IodideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 21502510[1-Methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethylamine

Product 1

HCID 21502450[1-Methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethyl(4-chlorobenzyl)ammonium iodideYield 131.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of [1-methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2-(trans)propenyl]dimethylamine (2.2 g), α,4-dichlorotoluene (0.8 g) and ethanol (30 cc) was refluxed for 1 hour, and thereto were added water (100 cc) and potassium iodide (5.0 g). The reaction mixture was extracted with chloroform, and the chloroform layer was dried over magnesium sulfate. The solvent was distilled off, and the residue was recrystallized from ethanol to give crystals (3.1 g) of [1-methyl-3-(2,6,6-trimethyl-2-cyclohexenyl)-2(trans)-propenyl]dimethyl(4-chlorobenzyl)ammonium iodide.

Workup

  1. temperaturewas refluxed for 1 hour
  2. extractionThe reaction mixture was extracted with chloroform
  3. dry with materialthe chloroform layer was dried over magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-1fafe0e295bc4256a85fda167ac6d9ca
Source dataset
uspto-grants-1976_10
Patent number
US03988373

Reaction notes

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